#------------------------------------------------------------------------------
#$Date: 2017-03-02 07:37:34 +0200 (Thu, 02 Mar 2017) $
#$Revision: 192754 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/20/2242039.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242039
loop_
_publ_author_name
'Kasyanova, Katerina V.'
'Kokozay, Vladimir N.'
'Buvaylo, Elena A.'
'Vassilyeva, Olga Yu.'
'Skelton, Brian W.'
_publ_section_title
;
 Crystal structure of
 4,10-dimethoxy-13-methyl-6H,12H-6,12-epiminodibenzo[b,f][1,5]dioxocine
;
_journal_coeditor_code           HG5482
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              410
_journal_page_last               412
_journal_paper_doi               10.1107/S2056989017002328
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C17 H17 N O4'
_chemical_formula_moiety         'C17 H17 N O4'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.31
_chemical_name_systematic
4,10-Dimethoxy-13-methyl-6H,12H-6,12-epiminodibenzo[b,f][1,5]dioxocine
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                93.980(6)
_cell_angle_beta                 106.603(7)
_cell_angle_gamma                102.133(6)
_cell_formula_units_Z            2
_cell_length_a                   6.9956(5)
_cell_length_b                   8.8589(6)
_cell_length_c                   12.0938(9)
_cell_measurement_reflns_used    2735
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.096
_cell_measurement_theta_min      3.857
_cell_volume                     695.46(9)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 1999) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
WinGX (Farrugia, 1999)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4738
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5235
_diffrn_reflns_theta_full        67.243
_diffrn_reflns_theta_max         67.242
_diffrn_reflns_theta_min         3.851
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.81756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0737P)²+0.1321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                2147
_reflns_number_total             2456
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hg5482sup1.cif
_cod_data_source_block           I
_cod_database_code               2242039
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.8680(3) 0.77719(18) 0.96792(13) 0.0272(4) Uani d 1
H H1A 1.0173 0.8034 1.0043 0.041 Uiso calc 1
H H1B 0.802 0.8059 1.0249 0.041 Uiso calc 1
H H1C 0.8334 0.8345 0.9014 0.041 Uiso calc 1
N N1 0.7947(2) 0.60859(15) 0.92762(11) 0.0239(3) Uani d 1
C C11 0.6973(2) 0.64283(16) 0.69544(13) 0.0208(3) Uani d 1
O O11 0.89314(15) 0.63442(12) 0.75392(9) 0.0216(3) Uani d 1
C C12 0.5341(2) 0.60187(17) 0.74052(13) 0.0220(3) Uani d 1
C C121 0.5761(2) 0.56411(17) 0.86455(13) 0.0234(3) Uani d 1
H H121 0.5042 0.624 0.9056 0.028 Uiso calc 1
C C13 0.3363(2) 0.60620(17) 0.67238(14) 0.0248(3) Uani d 1
H H13 0.2232 0.5779 0.7016 0.03 Uiso calc 1
C C14 0.3059(2) 0.65148(18) 0.56296(14) 0.0260(4) Uani d 1
H H14 0.1707 0.6494 0.5159 0.031 Uiso calc 1
C C15 0.4714(2) 0.70032(17) 0.52068(13) 0.0245(3) Uani d 1
H H15 0.4492 0.7351 0.4465 0.029 Uiso calc 1
C C16 0.6678(2) 0.69812(17) 0.58676(13) 0.0217(3) Uani d 1
O O16 0.84270(16) 0.74649(12) 0.55663(9) 0.0252(3) Uani d 1
C C161 0.8176(3) 0.80636(19) 0.44818(13) 0.0280(4) Uani d 1
H H16A 0.7297 0.7244 0.3846 0.042 Uiso calc 1
H H16B 0.9522 0.8411 0.4367 0.042 Uiso calc 1
H H16C 0.7536 0.8946 0.4488 0.042 Uiso calc 1
C C21 0.6140(2) 0.31265(18) 0.82770(12) 0.0214(3) Uani d 1
O O21 0.50055(16) 0.40035(12) 0.86700(9) 0.0242(3) Uani d 1
C C22 0.8031(2) 0.37774(17) 0.81425(12) 0.0215(3) Uani d 1
C C221 0.8989(2) 0.55005(17) 0.85422(13) 0.0218(3) Uani d 1
H H221 1.0459 0.563 0.9011 0.026 Uiso calc 1
C C23 0.9039(2) 0.28166(18) 0.76738(13) 0.0232(3) Uani d 1
H H23 1.033 0.3251 0.7573 0.028 Uiso calc 1
C C24 0.8164(2) 0.12416(18) 0.73579(13) 0.0241(3) Uani d 1
H H24 0.8838 0.0603 0.7017 0.029 Uiso calc 1
C C25 0.6289(2) 0.05727(18) 0.75355(13) 0.0235(3) Uani d 1
H H25 0.5711 -0.0517 0.7332 0.028 Uiso calc 1
C C26 0.5290(2) 0.15091(18) 0.80075(13) 0.0225(3) Uani d 1
O O26 0.34536(17) 0.10158(12) 0.82185(10) 0.0275(3) Uani d 1
C C261 0.2625(3) -0.06296(19) 0.80651(16) 0.0326(4) Uani d 1
H H26A 0.2318 -0.1056 0.7247 0.049 Uiso calc 1
H H26B 0.1359 -0.0843 0.8284 0.049 Uiso calc 1
H H26C 0.3628 -0.1118 0.8559 0.049 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C221 N1 C121 107.32(12)
C221 N1 C1 114.33(12)
C121 N1 C1 112.09(12)
O11 C11 C12 122.53(13)
O11 C11 C16 116.70(13)
C12 C11 C16 120.76(13)
C11 O11 C221 111.80(11)
C11 C12 C13 118.88(14)
C11 C12 C121 119.41(13)
C13 C12 C121 121.58(13)
O21 C121 N1 108.62(12)
O21 C121 C12 111.51(12)
N1 C121 C12 111.31(12)
O21 C121 H121 108.4
N1 C121 H121 108.4
C12 C121 H121 108.4
C14 C13 C12 120.10(14)
C14 C13 H13 120
C12 C13 H13 120
C13 C14 C15 120.80(14)
C13 C14 H14 119.6
C15 C14 H14 119.6
C16 C15 C14 119.99(14)
C16 C15 H15 120
C14 C15 H15 120
O16 C16 C15 125.65(14)
O16 C16 C11 115.10(13)
C15 C16 C11 119.24(14)
C16 O16 C161 116.22(11)
O16 C161 H16A 109.5
O16 C161 H16B 109.5
H16A C161 H16B 109.5
O16 C161 H16C 109.5
H16A C161 H16C 109.5
H16B C161 H16C 109.5
O21 C21 C22 122.61(14)
O21 C21 C26 116.68(13)
C22 C21 C26 120.72(14)
C21 O21 C121 111.48(11)
C21 C22 C23 119.15(14)
C21 C22 C221 119.33(13)
C23 C22 C221 121.48(13)
N1 C221 O11 111.99(12)
N1 C221 C22 109.13(12)
O11 C221 C22 110.50(11)
N1 C221 H221 108.4
O11 C221 H221 108.4
C22 C221 H221 108.4
C24 C23 C22 120.23(14)
C24 C23 H23 119.9
C22 C23 H23 119.9
C23 C24 C25 120.62(14)
C23 C24 H24 119.7
C25 C24 H24 119.7
C26 C25 C24 119.59(14)
C26 C25 H25 120.2
C24 C25 H25 120.2
O26 C26 C25 125.72(14)
O26 C26 C21 114.69(13)
C25 C26 C21 119.56(14)
C26 O26 C261 116.82(12)
O26 C261 H26A 109.5
O26 C261 H26B 109.5
H26A C261 H26B 109.5
O26 C261 H26C 109.5
H26A C261 H26C 109.5
H26B C261 H26C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.4716(19)
C1 H1A 0.98
C1 H1B 0.98
C1 H1C 0.98
N1 C221 1.433(2)
N1 C121 1.454(2)
C11 O11 1.3707(18)
C11 C12 1.394(2)
C11 C16 1.410(2)
O11 C221 1.4636(17)
C12 C13 1.403(2)
C12 C121 1.519(2)
C121 O21 1.4413(18)
C121 H121 1
C13 C14 1.381(2)
C13 H13 0.95
C14 C15 1.395(2)
C14 H14 0.95
C15 C16 1.382(2)
C15 H15 0.95
C16 O16 1.3675(19)
O16 C161 1.4271(18)
C161 H16A 0.98
C161 H16B 0.98
C161 H16C 0.98
C21 O21 1.3723(18)
C21 C22 1.387(2)
C21 C26 1.407(2)
C22 C23 1.399(2)
C22 C221 1.515(2)
C221 H221 1
C23 C24 1.379(2)
C23 H23 0.95
C24 C25 1.403(2)
C24 H24 0.95
C25 C26 1.381(2)
C25 H25 0.95
C26 O26 1.3690(19)
O26 C261 1.4286(18)
C261 H26A 0.98
C261 H26B 0.98
C261 H26C 0.98
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C13 H13 O11 1_455 0.95 2.69 3.5616(19) 152.1
C1 H1B O26 2_667 0.98 2.53 3.508(2) 175.6

_cod_database_fobs_code 2242039
